Substituted 3,4-dihydropyrido[1,2-a]pyrimidines

ABSTRACT

Substituted  3,4 -dihydropyrido[1,2-a]pyrimidines of formula I 
                         
and processes for the production thereof Also disclosed are substance libraries and pharmaceutical compositions containing the compound, and methods of treatment for pain, urinary incontinence, pruritus, tinnitus and/or diarrhoea using the pharmaceutical composition.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of International Patent Application No. PCT/EP01/11700, filed Oct. 10, 2001, designating the United States of America and published in German as WO 02/30933 A1, the entire disclosure of which is incorporated herein by reference. Priority is claimed based on Federal Republic of Germany Patent Application No. 100 50 662.3, filed Oct. 13, 2000.

FIELD OF THE INVENTION

The present application relates to substituted 3,4-dihydropyrido[1,2-a]pyrimidines, to processes for the production thereof, to substance libraries containing them, to pharmaceutical preparations containing these compounds, to the use of these compounds for the production of pharmaceutical preparations, and methods for the treatment of pain, urinary incontinence, pruritus, tinnitus and/or diarrhea and to pharmaceutical compositions containing these compounds.

BACKGROUND OF THE INVENTION

The treatment of chronic and non-chronic pain is of great significance in medicine. There is a worldwide requirement for effective therapeutic methods for providing tailored and targeted treatment of chronic and non-chronic pain, especially effective and satisfactory pain treatment from the patient's standpoint.

Conventional opioids such as morphine are highly effective in treating severe to very severe pain. However, their use is limited by known side-effects such as respiratory depression, vomiting, sedation, constipation and development of tolerance. Moreover, they are less effective in treating neuropathic or incidental pain, which is in particular experienced by tumor patients.

DESCRIPTION OF THE INVENTION

An object of the present invention is to provide analgesically active compounds suitable for pain therapy, in particular for treating chronic and neuropathic pain. Furthermore, these substances should as much as possible not cause any of the side-effects which occur when using opioids with P-receptor affinity (e.g. morphine), such as nausea, vomiting, dependency, respiratory depression or constipation.

This object is achieved by the compounds of the general formula I which are analgesically active. The compounds according to the invention comprise substituted 3,4-dihydropyrido[1,2-a]pyrimidines of the general formula I

in which

-   R¹ and R² mutually independently mean H; OR¹⁰; SH; SR¹⁰; C₁₋₁₂     alkyl, which is linear or branched and is saturated or unsaturated     and is unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl,     which is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted; aryl, which is unsubstituted or mono- or     polysubstituted; heteroaryl, which is unsubstituted or mono- or     polysubstituted, (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear     or branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted, and the aryl is unsubstituted or mono- or     polysubstituted; or (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl     is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, and the heteroaryl is     unsubstituted or mono- or polysubstituted,     -   wherein one of R¹ and R² is H and the other of R¹ and R² is not         H, provided that, if one of R¹ and R² means aryl, the other of         R¹ and R² means H or C₁₋₁₂ alkyl, -   R³ and R⁴ mutually independently mean H; C₁₋₁₂ alkyl, which is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, which is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted; aryl, which is unsubstituted or mono- or     polysubstituted; heteroaryl, which is unsubstituted or mono- or     polysubstituted; (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear     or branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted, and the aryl is unsubstituted or mono- or     polysubstituted; or (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl     is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, and the heteroaryl is     unsubstituted or mono- or polysubstituted,     -   wherein at least one of R³ and R⁴ is H, or -   one of R¹ or R², together with one of R³ or R⁴, forms W, wherein W     means α′-(CH₂)_(n)-β′ where n=3, 4, 5, 6, 7, 8, 9 or 10;     α′-CH═CH—CH₂-β′; α′-CH═CH—CH₂—CH₂-β′; α′-CH₂—CH═CH—CH₂-β′;     α′-CH₂—CH₂—CH═CH—CH₂—CH₂-β′; α′-O—(CH₂)_(n)-β′ where n=2, 3, 4, 5 or     6,

where X=CH₂, O or S;

and the end of W marked α′ is attached to the α carbon atom of the compound of the general formula I and the end of W marked β′ is attached to the β carbon atom of the compound of the general formula I,

-   -   the other of R¹ and R² is H or C₁₋₁₂ alkyl, wherein the alkyl is         linear or branched and is saturated or unsaturated and is         unsubstituted or mono- or polysubstituted, and the other of R³         and R⁴ is H or C₁₋₁₂ alkyl, wherein the alkyl is linear or         branched and is saturated or unsaturated and is unsubstituted or         mono- or polysubstituted,

-   R⁵ means C₁₋₁₂ alkyl, which is linear or branched and is saturated     or unsaturated and is unsubstituted or mono- or polysubstituted;     C₃₋₈ cycloalkyl, which is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, aryl, wherein aryl is     unsubstituted or mono- or polysubstituted; heteroaryl, which is     unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein     the C₁₋₆ alkyl is linear or branched and is saturated or unsaturated     and is unsubstituted or mono- or polysubstituted; and the aryl is     unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)heteroaryl,     wherein the C₁₋₆ alkyl is linear or branched and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, and     the heteroaryl is unsubstituted or mono- or polysubstituted,     C(═O)R¹¹, CO₂H or CO₂R¹²,

-   R⁶, R⁷, R8 and R⁹ mutually independently mean H, F, Cl, Br, I, CN,     NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl), N((C₁₋₆     alkyl)aryl)₂, NHR¹³, NO₂, OH, SH, O—C₁₋₈ alkyl or S(O)_(p)—C₁₋₈     alkyl, wherein the alkyl is linear or branched and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, and p     is 0, 1 or 2; O-aryl or S(O)_(q)-aryl, wherein the aryl is     unsubstituted or mono- or polysubstituted and q is 0, 1 or 2;     O—(C₁₋₆ alkyl)aryl or S(O)_(r)—(C₁₋₆ alkyl)aryl, wherein the C₁₋₆     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, and the aryl is     unsubstituted or mono- or polysubstituted and r is 0, 1 or 2; CO₂H,     C(═O)R¹⁴, C₁₋₁₂ alkyl, wherein the alkyl is linear or branched and     is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted; CF₃, C₃₋₈ cycloalkyl, wherein the cycloalkyl is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted; heterocyclyl, which is 3-, 4-, 5-, 6- or 7-membered     and is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted; aryl, which is unsubstituted or mono- or     polysubstituted; or heteroaryl, which is unsubstituted or mono- or     polysubstituted, or

-   R⁶ and R⁷ together form Q, wherein Q means     γ′-CR¹⁵═CR¹⁶—CR¹⁷═CR¹⁸-δ′, the end of Q marked γ′ is attached to the     γ carbon atom of the compound of the general formula I, and the end     of Q marked δ′ is attached to the δ carbon atom of the compound of     the general formula I, and R⁸ and R⁹ are defined as above, or

-   R⁶ and R⁹ together form T, wherein T means δ′-CR¹⁹═CR²⁰—CR²¹═CR²²-ε′     or γ′-N═CR²⁰—CR²¹═N-ε′, the end of T marked γ′ is attached to the γ     carbon atom of the compound of the general formula I and the end of     T marked ε′ is attached to the ε carbon atom of the compound of the     general formula I, and R⁷ and R⁸ are defined as above, or

-   R⁸ and R⁹ together form U, wherein U means     η′-CR¹⁹═CR²⁰—CR²¹═CR²²-ε′, the end of U marked η′ is attached to the     η carbon atom of the compound of the general formula I and the end     of U marked ε′ is attached to the ε carbon atom of the compound of     the general formula I, and R⁶ and R⁷ are defined as above,

-   R¹⁰ means C₁₋₈ alkyl, which is linear or branched and is saturated     or unsaturated and is unsubstituted or mono- or polysubstituted;     C₃₋₈ cycloalkyl, wherein cycloalkyl is saturated or unsaturated and     is unsubstituted or mono- or polysubstituted, aryl, which is     unsubstituted or mono- or polysubstituted, heteroaryl, which is     unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein     the C₁₋₆ alkyl is linear or branched and is saturated or unsaturated     and is unsubstituted or mono- or polysubstituted, and the aryl is     unsubstituted or mono- or polysubstituted; or (C₁₋₆     alkyl)heteroaryl, wherein the C₁₋₆ alkyl is linear or branched and     is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, and the heteroaryl is unsubstituted or mono- or     polysubstituted,

-   R¹¹ means NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl),     N((C₁₋₆ alkyl)aryl)₂, C₁₋₈ alkyl, wherein the alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted; or     mono- or polysubstituted, C₃₋₈ cycloalkyl, which is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted; aryl,     which is unsubstituted or mono- or polysubstituted; heteroaryl,     which is unsubstituted or mono- or polysubstituted, (C₁₋₆     alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, and the aryl is unsubstituted or mono- or     polysubstituted; or (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl     is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, and the heteroaryl is     unsubstituted or mono- or polysubstituted,

-   R¹² means C₁₋₈ alkyl, which is linear or branched and is saturated     or unsaturated and is unsubstituted or mono- or polysubstituted;     C₃₋₈ cycloalkyl, which is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein     the C₁₋₆ alkyl is linear or branched and is saturated or unsaturated     and is unsubstituted or mono- or polysubstituted, and the aryl is     unsubstituted or mono- or polysubstituted,

-   R¹³ means C(═O)CH₃, C(═O)phenyl, C(═O)O-t.-butyl (t-BOC) or another     conventional amino protective group,

-   R¹⁴ means H, NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆     alkyl)aryl), N((C₁₋₆ alkyl)aryl)₂, C₁₋₈ alkyl, wherein the alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, which is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted; aryl, which is unsubstituted or mono- or     polysubstituted; or (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, and the aryl is     unsubstituted or mono- or polysubstituted; OC₁₋₈ alkyl, wherein the     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted; OC₃₋₈ cycloalkyl, wherein     the cycloalkyl is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted; O-aryl, wherein the aryl is unsubstituted     or mono- or polysubstituted; or O—(C₁₋₆ alkyl)aryl, wherein the C₁₋₆     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, and the aryl is     unsubstituted or mono- or polysubstituted,

-   R¹⁵, R¹⁶, R¹⁷ and R¹⁸ mutually independently mean H, F, Cl, Br, I,     CN, OH, C₁₋₈ alkyl, wherein the alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, or CO₂H, and

-   R¹⁹, R²⁰, R²¹ and R²² mutually independently mean H, F, Cl, Br, I,     CN, OH, C₁₋₈ alkyl, wherein the alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, or CO₂H,     or the pharmaceutically acceptable salts thereof.

The following compounds of the general formula I are already known in the prior art, without the use thereof having been described in a pharmaceutical preparation or for the production of a pharmaceutical preparation for the treatment of pain, urinary incontinence, pruritus, tinnitus and/or diarrhea. These known compounds include 6-chloro-2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(2-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-(4-tolyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine and 2-(4-chlorophenyl)-(4-(4-tolyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, which have been described by M. A. Abdel-Rahman, Revue Roumaine de Chimie 40, 535–540 (1995); 4-ethoxy-2-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine and 4-ethoxy-2-(2-hydroxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, which have been described by L. S. Povarov, Chem. Heterocycl. Comp. 15, 1369 (1979) (C. A. 92 (1980), 110889); 4-ethoxy-2-propyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimdinem, 4-propyl-2,3,3a,4,5,10a-hexahydro-2H-pyrido[1,2-a]furo[3,2-e]pyrimidine and 4-propyl-2,4,4a,5,6,11a-hexahydro-2H-pyrido[1,2-a]pyrano[3,2-e]pyrimidine, which have been described by A. R. Katritzky, G Qin, B. Yang, Synthesis 1998, 704–706.

For the purposes of the present invention, the terms “C₁₋₆ alkyl”, “C₁₋₈ alkyl” and “C₁₋₁₂ alkyl” comprise acyclic saturated or unsaturated hydrocarbon residues, which may be branched or linear and unsubstituted or mono- or polysubstituted, respectively comprising 1 to 6, 1 to 8 and 1 to 12 carbon atoms, i.e. C₁₋₆ alkanyls, C₂₋₆ alkenyls and C₂₋₆ alkynyls, C₁₋₈ alkanyls, C₂₋₈ alkenyls and C₂₋₈ alkynyls and C₁₋₁₂ alkanyls, C₂₋₁₂ alkenyls and C₂₋₁₂ alkynyls. Alkenyls here comprise at least one C—C double bond and alkynyls at least one C—C triple bond. Alkyl is advantageously selected from the group comprising methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-pentyl, iso-pentyl, neopentyl, n-hexyl, 2-hexyl, n-octyl, n-decyl, n-dodecyl; ethylenyl (vinyl), ethynyl, propenyl (—CH₂CH═CH₂, —CH═CH—CH₃, —C(═CH₂)—CH₃propynyl,(—CH—C═CH), butenyl, butynyl, pentenyl, hexenyl, hexynyl, octenyl and octynyl.

For the purposes of the present invention, the term “C₃₋₈ cycloalkyl” means cyclic hydrocarbons with 3 to 8 carbon atoms, which may be saturated or unsaturated, unsubstituted or mono- or polysubstituted. C₃₋₈ cycloalkyl is advantageously selected from the group which contains cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl. Cyclopropyl, cyclopropyl-2-carboxylic acid, cyclopropyl-2-carboxylic acid ethyl ester and cyclohexyl are particularly preferred for thr purposes of the present invention.

For the purposes of the present invention, the term “aryl” means aromatic hydrocarbons, inter alia phenyls, naphthyls and anthracenyls. The aryl residue may also be fused with further saturated, (partially) unsaturated or aromatic ring systems. Each aryl residue may be present in unsubstituted or mono-or polysubstituted form, wherein the aryl substituets may be identical or different and be in any desired position of the aryl. Aryl is advantageously selected from the group which contains phenyl, 1-naphthyl and 2-naphthyl. For thr purposes of the invention, particularly preferred aryl residues are m-toluyl, p-hydroxyphenyl, p-methoxyphenyl, 4-hydroxy-3-methoxyphenyl, 2,4-dimethylphenyl, 4-fluorophenyl, 1-naphthyl and 2-naphthyl.

The term “heteroaryl” denotes a 5-, 6- or 7-membered cyclic aromatic residue, which contains at least 1, optionally also 2, 3, 4 or 5 heteroatoms, wherein the heteroatoms are identical or different and the heterocycle may be unsubstituted or mono- or polysubstituted; in the event of substitution on the heterocycle, the heteroaryl substituents may be identical or different and be in any possible position of the heteroaryl. The heterocycle may also be part of a bi- or polycyclic system. Preferred heteroatoms are nitrogen, oxygen and sulfur. It is preferred for the heteroaryl to be selected from among the group comprising pyrrolyl, indolyl, furyl (furanyl), benzofuranyl, thienyl (thiophenyl), benzothienyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isoxazoyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyranyl, indolyl, indazolyl, purinyl, pyrimidinyl, indolizinyl, quinolinyl, isoquinolyl, quinazolinyl, carbazolyl, phenazinyl, phenothiazinyl, wherein the bond to the compounds of the general formula I (or II, III or IV) may be made via any desired and possible ring member of the heteroaryl residue. For the purposes of the present invention, particularly preferred heteroaryl residues are 2-pyridinyl, 2-furanyl, 5-methyl-2-furanyl and 5-nitro-2-furanyl.

For the purposes of the present invention, the terms “(C₁₋₆ alkyl)aryl” and “(C₁₋₆ alkyl)heteroaryl” mean that C₁₋₆ alkyl, aryl and heteroaryl have the above-defined meanings and are attached via a C₁₋₆ alkyl group to the compound of the general formula I (or II, III or IV).

The term “heterocyclyl” denotes a 3-, 4-, 5-, 6- or 7-membered cyclic organic residue, which contains at least 1, optionally also 2, 3, 4 or 5 heteroatoms, wherein the heteroatoms are identical or different and the cyclic residue is saturated or unsaturated, but not aromatic, and may be unsubstituted or mono- or polysubstituted. The heterocycle may also be part of a bi- or polycyclic system. Preferred heteroatoms are nitrogen, oxygen and sulfur. It is preferred that the heterocyclyl residue is selected from among the group which contains tetrahydrofuryl, pyrrolidinyl, piperidinyl, piperazinyl and morpholinyl, wherein the bond to the compound of the general formula I (or II, III or IV) may be made via any desired ring member of the heterocyclyl residue.

In connection with “alkyl”, “alkanyl”, “alkenyl” and “alkynyl”, the term “substituted” is taken for the purposes of the present invention to mean the substitution of a hydrogen residue by F, Cl, Br, I, CN, NH₂, NH-alkyl, NH-aryl, heteroaryl, NH-alkylaryl, NH-alkylheteroaryl, NH-heterocyclyl, NH-alkyl-OH, N(alkyl)₂, N(alkylaryl)₂, N(alkylheteroaryl)₂, N(heterocyclyl)₂, N(alkyl-OH)₂, NO, NO₂, SH, S-alkyl, S-aryl, S-heteroaryl, S-alkylaryl, S-alkylheteroaryl, S-heterocyclyl, S-alkyl-OH, S-alkyl-SH, OH, O-alkyl, O-aryl, O-heteroaryl, O-alkylaryl, O-alkylheteroaryl, O-heterocyclyl, O-alkyl-OH, CHO, C(═O)C₁₋₆ alkyl, C(═S)C₁₋₆ alkyl, C(═O) aryl, C(═S) aryl, C(═O)C₁₋₆ alkylaryl, C(═S)C₁₋₆ alkylaryl, C(═O) heteroaryl, C(═S) heteroaryl, C(═O) heterocyclyl, C(═S) heterocyclyl, CO₂H, CO₂ alkyl, C(═O)NH_(2,) C(═O)NH alkyl, C(═O)NH aryl, C(═O)NH heterocyclyl, C(═O)N(alkyl)₂, C(═O)N(alkylaryl)₂, C(═O)N(alkylheteroaryl)₂, C(═O)N(heterocyclyl)₂, SO alkyl, SO₂ alkyl, SO₂NH₂, SO₃H, cycloalkyl, aryl, heteroaryl or heterocyclyl. Polysubstituted residues should be taken to mean such residues which are substituted more than once either on the same or on different atoms, for example are di- or trisubstituted, for example three times on the same C atom, as in the case of CF₃ or —CH₂CF₃ or at different sites, as in the case of —CH(OH)—CH═CH—CHCl₂. Polysubstitution may proceed with identical or different substituents. For the purposes of the invention, methyl, ethyl, n-propyl, —CH₂—CH₂—OH or CF₃ are particularly preferred.

With regard to “aryl”, “alkylaryl”, “heteroaryl”, “alkylheteroaryl”, “heterocyclyl”, and “cycloalkyl”, “mono- or polysubstituted” is taken for the purposes of the present invention to mean mono- or polysubstitution, e.g. di-, tri- or tetrasubstitution of one or more hydrogen atoms of the ring system by F, Cl, Br, I, CN, NH₂, NH-alkyl, NH-aryl, NH-heteroaryl, NH-alkylaryl, NH-alkylheteroaryl, NH-heterocyclyl, NH-alkyl-OH, N(alkyl)₂, N(alkylaryl)₂, N(alkylheteroaryl)₂, N(heterocyclyl)₂, N(alkyl-OH)₂, NO, NO₂, SH, S-alkyl, S-cycloalkyl, S-aryl, S-heteroaryl, S-alkylaryl, S-alkylheteroaryl, S-heterocyclyl, S-alkyl-OH, S-alkyl-SH, OH, O-alkyl, O-cycloalkyl, O-aryl, O-heteroaryl, O-alkylaryl, O-alkylheteroaryl, O-heterocyclyl, O-alkyl-OH, CHO, C(═O)C₁₋₆ alkyl, C(═S)C₁₋₆ alkyl, C(═O) aryl, C(═S) aryl, C(═O)—C₁₋₆ alkylaryl, C(═S)C₁₋₆ alkylaryl, C(═O) heteroaryl, C(═S) heteroaryl, C(═O) heterocyclyl, C(═S) heterocyclyl, CO₂H, CO₂ alkyl, C(═O)NH₂, C(═O)NH-alkyl, C(═O)NH aryl, C(═O)NH heterocyclyl, C(═O)N(alkyl)₂, C(═O)N(alkylaryl)₂, C(═O)N(alkylheteroaryl)₂, C(═O)N(heterocyclyl)₂, S(O) alkyl, S(O) aryl, SO₂ alkyl, SO₂ aryl, SO₂NH₂, SO₃H, cycloalkyl, aryl, heteroaryl, CF₃, ═O, ═S; C₁₋₆-alkanyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, —C₁₋₆ alkyl-C(O)O—C₁₋₆ alkyl; phenyl, benzyl, naphthyl and/or heterocyclyl; on one or optionally different atoms (wherein a substituent may optionally in turn itself be substituted). Polysubstitution may be with identical or different substituents. Particularly preferred substituents for aryl are F, OH, CH₃ and OCH₃. Particularly preferred substituents for heteroaryl are CH₃ and NO₂. Particularly preferred substituents for cycloalkyl are CO₂H and CO₂-ethyl.

For the purposes of the present invention, pharmaceutically acceptable salts are those salts of the compounds according to the invention of the general formula I which are physiologically compatible for pharmaceutical use, in particular for use in mammals, especially humans. Such pharmaceutically acceptable salts may, for example, be formed with inorganic or organic acids.

The pharmaceutically acceptable salts of the compounds according to the invention of the general formula I are preferably formed with hydrochloric acid, hydrobromic acid, sulfuiric acid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid, carbonic acid, formic acid, acetic acid, oxalic acid, succinic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, glutamic acid or aspartic acid. The salts formed comprise, inter alia, hydrochlorides, hydrobomides, phosphates, carbonates, hydrogencarbonates, formates, acetates, oxalates, succinates, tartrates, fumarates, citrates and glutamates. The hydrates of the compounds according to the invention, which may be obtained, for example, by crystallization from an aqueous solution, are also preferred.

All the compounds according to the invention contain at least one center of asymmetry, namely the R⁵-substituted carbon atom of the structure I. The compound according to the invention of the general formula I may accordingly assume the form of a racemate, of a pure enantiomer or a diastereomer, or of a mixture of the enantiomer, or diastereomer as a free substance, or as the pharmaceutically acceptable salts of these compounds. The mixtures may be present in any desired mixture ratio of the stereoisomers. The compounds of the general formula I are preferably present as enantiomerically pure compounds.

Preferred compounds of the present invention are 3,4-dihydropyrido[1,2-a]pyrimidines of the general formula I, in which one of the residues R¹ and R² means OR¹⁰, SR¹⁰, C₁₋₆ alkyl or aryl, one of the residues R³ and R⁴ means H or C₁₋₆ alkyl, or one of R¹ and R²

together with one of R³ and R⁴ form W, wherein W means

and the other two residues of R¹, R², R³ and R⁴ mean H or C₁₋₆ alkyl, R⁵ means C₃₋₆ cycloalkyl, heteroaryl, C(═O)R¹¹, CO₂H or CO₂R¹², R⁶ means H, F, Cl, Br, CN, NO₂, C(═O)R¹⁴, C₁₋₆ alky, CF₃ or aryl, R⁷ means H, F, Cl, Br, CN, NH₂, OH or C₁₋₆ alkyl, or R⁶ and R⁷ together form Q, wherein Q means γ′-CR¹⁵═CR¹⁶—CR¹⁷═CR¹⁸-δ′, R⁸ means H, F, Cl, Br, CN, NO₂, O—(C₁₋₆ alkyl)aryl, CO₂H, CONH₂ or C₁₋₆ alkyl, R⁹ means H, OH, CF₃ or C₁₋₆ alkyl, or R⁸ and R⁹ together form U, wherein U means ε′-CH═CH—CH═CH-η′, R¹⁰ means C₁₋₈ alkyl or aryl, R¹¹ means aryl, R¹² means C₁₋₆ alkyl, R¹⁴ means OC₁₋₆ alkyl, one or R¹⁵, R¹⁶, R¹⁷ and R¹⁸ means H or OH and the other residues of R¹⁵, R¹⁶, R¹⁷ and R¹⁸ mean H, and the pharmaceutically acceptable salts thereof.

Particularly preferred compounds of the general formula I are those in which one of the residues R¹ and R² means O—(CH₂)₂—OH, S-phenyl, CH₃, phenyl, 3-methylphenyl, 2,4-dimethylphenyl, 4-fluorophenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 4-hydroxy-3-methoxyphenyl or 2-naphthyl, one of the residues R³ and R⁴ means H or methyl, or one of R¹ and

R² together with one of R³ and R⁴ form W, wherein W means

and the other two residues of R¹, R², R³ and R⁴ mean H, R⁵ means cyclopropyl, 2-(C(═O)O-ethyl)-cyclopropyl, cyclohexyl, 2-pyridinyl, 5-methyl-2-furanyl, 5-nitro-2-furanyl, C(═O)phenyl, CO₂H or CO₂ethyl, R⁶ means H, Cl, Br, CN, NO₂, CO₂ethyl, methyl, CF₃ or phenyl, R⁷ means H, Cl, CN, NH₂, OH, methyl or n-propyl, or R⁶ and R⁷ together form Q, wherein Q means γ′-CH═CH—CH═CR¹⁸-δ′, R⁸ means H, Cl, Br, NO₂, OH, O—CH₂phenyl, CO₂H or methyl, R⁹ means H or methyl, or R⁸ and R⁹ together form U, wherein U means ε′-CH═CH—CH═CH-η′, and R¹⁸ means H or OH, and the pharmaceutically acceptable salts thereof.

Highly preferred compounds according to the invention are those which are selected from among:

-   -   9-chloro-4-(4-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   9-chloro-4-(4-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7-bromo-4-(4-methoxyphenyl)-9-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dichloro-4-(3,4-dimethoxyphenyl)-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-4-(3,4-dimethoxyphenyl)-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   4-(3,4-dimethoxyphenyl)-7-nitro-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dichloro-4-(4-methoxyphenyl)-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   2-[7,9-dichloro-4-(2,4-dimethylphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-2-yl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[9-chloro-4-(2,4-dimethylphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-2-yl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[7,9-dibromo-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[9-chloro-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   4-(4-hydroxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   7,9-dichloro-4-phenylsulfanyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7-nitro-4-phenylsulfanyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dichloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   9-chloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dichloro-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-methoxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   9-chloro-4-(4-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   4-(4-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7-bromo-4-(4-methoxyphenyl)-3-methyl-9-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dichloro-4-(4-hydroxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-hydroxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   9-chloro-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   [7,9-dichloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [4-(4-hydroxy-3-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [4-(4-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [7,9-dibromo-4-(4-hydroxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   [4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone,     -   2-(7,9-dichloro-2-cyclopropyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   2-(7,9-dibromo-2-cyclopropyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   2-(9-chloro-2-cyclopropyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   2-(2-cyclopropyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   9-chloro-2-cyclopropyl-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-2-cyclopropyl-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   9-chloro-2-cyclopropyl-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   2-cyclopropyl-4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   2-(7,9-dichloro-2-cyclohexyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   2-(7,9-dibromo-2-cyclohexyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   2-(7,9-dibromo-2-cyclohexyl-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   2-(9-chloro-2-cyclohexyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   2-(2-cyclohexyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol,     -   7,9-dichloro-2-cyclohexyl-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dichloro-2-cyclohexyl-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-2-cyclohexyl-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   9-chloro-2-cyclohexyl-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid ethyl ester,     -   7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine         2-carboxylic acid,     -   7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   2-[7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   4-(4-methoxyphenyl)-7-nitro-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   2-[7,9-dibromo-4-(2,4-dimethylphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[7,9-dibromo-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   2-[4-(4-fluorophenyl)-4-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane         carboxylic acid ethyl ester,     -   9-benzyloxy-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   8-methyl-7-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dichloro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   9-chloro-4-phenyl-2-pyridin-2-yl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   8-methyl-9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7-bromo-9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-6-methyl-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-9-carboxylic         acid,     -   7-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   9-benzyloxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   8-methyl-7-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   6-chloro-9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dichloro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   9-chloro-4-phenylsulfanyl-2-pyridin-2-yl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   8-methyl-9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7-bromo-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7-bromo-9-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]-9-pyrimidinol,     -   7-chloro-4-phenyisulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   4-phenylsulfanyl-6-propyl-2-pyridine-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-6-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyridol[1,2-a]pyrimidine,     -   4-phenylsulfanyl-2-pyridin-2-yl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   7,9-dibromo-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine,     -   1-phenylsulfanyl-3-pyridin-2-yl-2,3-dihydro-1H-pyrimidine[1,2-a]-10-quinolinol,     -   2-methyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   2,4-dichloro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   4-chloro-6-pyridin-2-yl-2-trifluoromethyl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   2-nitro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   4-nitro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   2-chloro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   1-propyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   2,4-dibromo-1-methyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   6-pyridin-2-yl-2-trifluoromethyl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline,     -   1,4-methano-5-pyridin-2-yl-1,4a,5,12c-tetrahydro-4H-6,12b-diaza-benzo[c]-12-phenathrenol,     -   1,4-methano-5-pyridin-2-yl-1,4a,5,12c-tetrahydro-4H-6,12b-diaza-benzo[c]phenathrene,         and     -   6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-isoquino[2,1-a]quinazoline,         and the pharmaceutically acceptable salts thereof.

The invention also relates to a process for the production of the compounds according to the invention of the general formula I

in which

-   R¹ and R² mutually independently mean H, OR¹⁰, SH, SR¹⁰, C₁₋₁₂     alkyl, wherein alkyl is linear or branched and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, C₃₋₈     cycloalkyl, wherein cycloalkyl is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, aryl, wherein aryl is     unsubstituted or mono- or polysubstituted, heteroaryl, wherein     heteroaryl is unsubstituted or mono- or polysubstituted, (C₁₋₆     alkyl)aryl, wherein C₁₋₆ alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, wherein one of R¹ and R²     is H and the other of R¹ and R² is not H, providing that, if one of     R¹ and R² means aryl, the other of R¹ and R² means H or C₁₋₁₂ alkyl, -   R³ and R⁴ mutually independently mean H, C₁₋₁₂ alkyl, wherein C₁₋₁₂     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, C₃₋₈ cycloalkyl, wherein     cycloalkyl is saturated or unsaturated and is unsubstituted or mono-     or polysubstituted, aryl, wherein aryl is unsubstituted or mono- or     polysubstituted, heteroaryl, wherein heteroaryl is unsubstituted or     mono- or polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and aryl is unsubstituted     or mono- or polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, wherein at least one of     R³ and R⁴ is H, or -   one of R¹ or R², together with one of R³ or R⁴, forms W, wherein W     means α′-(CH₂)_(n)-β′where n=3, 4, 5, 6, 7, 8, 9 or 10,     α′-CH═CH—CH₂-β′, α′-CH═CH—CH₂—CH₂-β′, α′-CH₂—CH═CH—CH₂-β′,     α′-CH₂—CH₂—CH═CH—CH₂—CH₂-β′, α′-O—(CH₂)_(n)-β′ where n=2, 3, 4, 5 or     6,

where X═CH₂, O or S,

and the end of W marked α′ is attached to the α carbon atom of the compound of the general formula I and the end of W marked β′ is attached to the β carbon atom of the compound of the general formula I, the other of R¹ and R² is H or C₁₋₁₂ alkyl, wherein alkyl is linear or branched and is saturated or unsaturated and is unsubstituted or mono- or polysubstituted, and the other of R³ and R⁴ is H or C₁₋₁₂ alkyl, wherein alkyl is linear or branched and is saturated or unsaturated and is unsubstituted or mono- or polysubstituted,

-   R⁵ means C₁₋₁₂ alkyl, wherein C₁₋₁₂ alkyl is linear or branched and     is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, aryl,     wherein aryl is unsubstituted or mono- or polysubstituted,     heteroaryl, wherein heteroaryl is unsubstituted or mono- or     polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, C(═O)R¹¹, CO₂H or CO₂R¹², -   R⁶, R⁷, R⁸ and R⁹ mutually independently mean H, F, Cl, Br, I, CN,     NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl), N((C₁₋₆     alkyl)aryl)₂, NHR¹³, NO₂, OH, SH, O—C₁₋₈ alkyl or S(O)_(p)—C₁₋₈     alkyl, wherein alkyl is linear or branched and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted and p     is 0, 1 or 2, O-aryl or S(O)_(q)-aryl, wherein aryl is unsubstituted     or mono- or polysubstituted and q is 0, 1 or 2, O—(C₁₋₆ alkyl)aryl     or S(O)_(r)—(C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted and r is 0, 1 or 2, CO₂H, C(═O)R¹⁴, C₁₋₁₂ alkyl,     wherein alkyl is linear or branched and is saturated or unsaturated     and is unsubstituted or mono- or polysubstituted, CF₃, C₃₋₈     cycloalkyl, wherein cycloalkyl is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, heterocyclyl, wherein     heterocyclyl is 3-, 4-, 5-, 6- or 7-membered and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, aryl,     wherein aryl is unsubstituted or mono- or polysubstituted, or     heteroaryl, wherein heteroaryl is unsubstituted or mono- or     polysubstituted, or R⁶ and R⁷ together form Q, wherein Q means     γ′-CR¹⁵═CR¹⁶—CR¹⁷═CR¹⁸-δ′, the end of Q marked γ′ is attached to the     γ carbon atom of the compound of the general formula I and the end     of Q marked δ′ is attached to the δ carbon atom of the compound of     the general formula I, and R⁸ and R⁹ are defined as above, or R⁶ and     R⁹ together form T, wherein T means γ′-CR¹⁹═CR²⁰—CR²¹═CR²²-ε′ or     γ′-N═CR²⁰—CR²¹═N-ε′, the end of T marked γ′ is attached to the γ     carbon atom of the compound of the general formula I and the end of     T marked ε′ is attached to the ε carbon atom of the compound of the     general formula I, and R⁷ and R⁸ are defined as above, or R⁸ and R⁹     together form U, wherein U means η′-CR¹⁹═CR²⁰—CR²¹═CR²²-ε′, the end     of U marked η′ is attached to the η carbon atom of the compound of     the general formula I and the end of U marked ε′ is attached to the     ε carbon atom of the compound of the general formula I, and R⁶ and     R⁷ are defined as above, -   R¹⁰ means C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, aryl,     wherein aryl is unsubstituted or mono- or polysubstituted,     heteroaryl, wherein heteroaryl is unsubstituted or mono- or     polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, -   R¹¹ means NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl),     N((C₁₋₆ alkyl)aryl)₂, C₁₋₈ alkyl, wherein alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, aryl, wherein aryl is unsubstituted or mono- or     polysubstituted, heteroaryl, wherein heteroaryl is unsubstituted or     mono- or polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and aryl is unsubstituted     or mono- or polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, -   R¹² means C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, (C₁₋₆     alkyl)aryl, wherein C₁₋₆ alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, -   R¹³ means C(═O)CH₃, C(═O)phenyl, C(═O)O-t.-butyl (t-BOC) or any     other conventional amino protective group, -   R¹⁴ means H, NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆     alkyl)aryl), N((C₁₋₆ alkyl)aryl)₂, C₁₋₈ alkyl, wherein alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, C₃₋₈ cycloalkyl, wherein     cycloalkyl is saturated or unsaturated and is unsubstituted or mono-     or polysubstituted, aryl, wherein aryl is unsubstituted or mono- or     polysubstituted, or (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear     or branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, OC₁₋₈ alkyl, wherein alkyl is linear or branched     and is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, OC₃₋₈ cycloalkyl, wherein cycloalkyl is saturated     or unsaturated and is unsubstituted or mono- or polysubstituted,     Oaryl, wherein aryl is unsubstituted or mono- or polysubstituted, or     O—(C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, -   R¹⁵, R¹⁶, R¹⁷ and R¹⁸ mutually independently mean H, F, Cl, Br, I,     CN, OH, C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, or CO₂H, and -   R^(19,) R²⁰, R²¹ and R²² mutually independently mean H, F, Cl, Br,     I, CN, OH, C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, or CO₂H,     and the pharmaceutically acceptable salts thereof,     wherein the process is characterized in that a heteroarylamine of     the general formula II

in which

-   R⁶ and R⁷ are defined as above, providing that, if R⁶ and R⁷ form Q     as defined above, the end of Q marked γ′ is attached to the γ carbon     atom of the heteroarylamine of the general formula II and the end of     Q marked δ′ is attached to the δ carbon atom of the heteroarylamine     of the general formula II, that R⁶ and R⁹ form T as defined above,     the end marked γ′ is attached to the γ carbon atom of the     heteroarylamine of the general formula II and the end marked ε′ is     attached to the ε carbon atom of the heteroarylamine of the general     formula II, and that R⁸ and R⁹ form U as defined above, the end     marked η′ is attached to the η carbon atom of the heteroarylamine of     the general formula II and the end marked ε′ is attached to the ε     carbon atom of the heteroarylamine of the general formula II,     is reacted in the presence of an acid with an aldehyde of the     general formula III

in which R⁵ is defined as above, and an olefin of the general formula IV

in which

-   R¹, R², R³ and R⁴ are defined as above, providing that, if one of     the residues R¹ and R², together with one of residues R³ and R⁴,     forms W, the end of W marked α′ is attached to the α carbon atom of     the olefin of the general formula IV and the end of W marked β′ is     attached to the β carbon atom of the olefin of the general formula     IV.

The process according to the invention is preferably performed in a “single-vessel” reaction, in which one heteroarylamine of the general formula II, one aldehyde of the general formula III and one olefin of the general formula IV are simultaneously reacted together.

The process according to the invention may also be performed in semi- or fully automated form as a parallel synthesis of a group of compounds according to the invention of the general formula I.

The acid used may be an inorganic or organic protonic or Lewis acid. The reaction is preferably performed in the presence of an organic acid, for example acetic acid, trifluoroacetic acid or methanesulfonic acid, in particular trifluoroacetic acid.

The process according to the invention may be performed in any suitable solvent in which the reactants are adequately soluble. Preferred solvents are organic solvents, for example dichloromethane or in particular acetonitrile.

The production according to the invention of the compounds according to the invention of the general formula I conveniently proceeds at a temperature of 0 to 100° C., in particular at 15 to 40° C. The reaction time is preferably 15 minutes to 12 hours and may be tailored to the requirements of the particular case.

The heteroarylamines of the general formula II, the aldehydes of the general formula III and the olefins of the general formula IV used in the process according to the invention are commercially obtainable (from Acros, Geel; Avocado, Port of Heysham; Aldrich, Deisenhofen; Fluka, Seelze; Lancaster, Mülheim; Maybridge, Tintagel; Merck, Darmstadt; Sigma, Deisenhofen; TCI, Japan) or may be produced using processes generally known to a person of ordinary skills in the art.

The compounds according to the invention of the general formula I may be isolated both as a free base and as a salt. The free base of the compound of the general formula I is conventionally obtained after completion of the above-described process according to the invention and subsequent conventional working up. The base obtained in said manner may then be converted into the corresponding salt for example by reaction with an inorganic or organic acid, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid, carbonic acid, formic acid, acetic acid, oxalic acid, succinic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, glutamic acid or aspartic acid. The salts formed comprise, inter alia, hydrochlorides, hydrobomides, phosphates, carbonates, hydrogencarbonates, formates, acetates, oxalates, succinates, tartrates, fumarates, citrates and glutamates. Formation of the particularly preferred hydrochloride may in particular also be achieved by combining the base, dissolved in a suitable solvent, with trimethylsilyl chloride (TMSCl).

Where the compounds of the general formula I are obtained in the production process according to the invention as racemates or as mixtures of the various enantiomers and/or diastereomers thereof, these mixtures may be separated using processes well known to the ordinarily skilled person in the art. Suitable methods are, inter alia, chromatographic separation processes, in particular liquid chromatography processes under standard or elevated pressure, preferably MPLC and HPLC processes, as well as fractional crystallization processes. Individual enantiomers may here in particular be separated from one another for example by means of HPLC on a chiral phase or by means of crystallization with chiral acids, such as (+)-tartaric acid, (−)-tartaric acid or (+)-10-camphorsulfonic acid.

The present invention also provides a substance library, which contains at least one compound of the general formula I

in which

-   R¹ and R² mutually independently mean H, OR¹⁰, SH, SR¹⁰, C₁₋₁₂     alkyl, wherein alkyl is linear or branched and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, C₃₋₈     cycloalkyl, wherein cycloalkyl is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, aryl, wherein aryl is     unsubstituted or mono- or polysubstituted, heteroaryl, wherein     heteroaryl is unsubstituted or mono- or polysubstituted, (C₁₋₆     alkyl)aryl, wherein C₁₋₆ alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, wherein one of R¹ and R²     is H and the other of R¹ and R² is not H, providing that, if one of     R¹ and R² means aryl, the other of R¹ and R² means H or C₁₋₁₂ alkyl, -   R³ and R⁴ mutually independently mean H, C₁₋₁₂ alkyl, wherein C₁₋₁₂     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, C₃₋₈ cycloalkyl, wherein     cycloalkyl is saturated or unsaturated and is unsubstituted or mono-     or polysubstituted, aryl, wherein aryl is unsubstituted or mono- or     polysubstituted, heteroaryl, wherein heteroaryl is unsubstituted or     mono- or polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and aryl is unsubstituted     or mono- or polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, wherein at least one of     R³ and R⁴ is H, or -   one of R¹ or R², together with one of R³ or R⁴, forms W, wherein W     means α′-(CH₂)_(n)-β′ where n=3, 4, 5, 6, 7, 8, 9 or 10,     α′-CH═CH—CH₂-β′, α′-CH═CH—CH₂—CH₂-β′, α′-CH₂—CH═CH—CH₂-β′,     α′-CH₂—CH₂—CH═CH—CH₂—CH₂-β′, α′-O—(CH₂)_(n)-β′ where n=2, 3, 4, 5 or     6,

where X═CH₂, O or S,

and the end of W marked α′ is attached to the α carbon atom of the compound of the general formula I and the end of W marked β′ is attached to the β carbon atom of the compound of the general formula I, the other of R¹ and R² is H or C₁₋₁₂ alkyl, wherein alkyl is linear or branched and is saturated or unsaturated and is unsubstituted or mono- or polysubstituted, and the other of R³ and R⁴ is H or C₁₋₁₂ alkyl, wherein alkyl is linear or branched and is saturated or unsaturated and is unsubstituted or mono- or polysubstituted,

-   R⁵ means C₁₋₁₂ alkyl, wherein C₁₋₁₂ alkyl is linear or branched and     is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, aryl,     wherein aryl is unsubstituted or mono- or polysubstituted,     heteroaryl, wherein heteroaryl is unsubstituted or mono- or     polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, C(═O)R¹¹, CO₂H or CO₂R¹², -   R⁶, R⁷, R⁸ and R⁹ mutually independently mean H, F, Cl, Br, I, CN,     NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl), N((C₁₋₆     alkyl)aryl)₂, NHR¹³, NO₂, OH, SH, O—C₁₋₈ alkyl or S(O)_(p)—C₁₋₈     alkyl, wherein alkyl is linear or branched and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted and p     is 0, 1 or 2, O-aryl or S(O)_(q)-aryl, wherein aryl is unsubstituted     or mono- or polysubstituted and q is 0, 1 or 2, O—(C₁₋₆ alkyl)aryl     or S(O)_(r)—(C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted and r is 0, 1 or 2, CO₂H, C(═O)R¹⁴, C₁₋₁₂ alkyl,     wherein alkyl is linear or branched and is saturated or unsaturated     and is unsubstituted or mono- or polysubstituted, CF₃, C₃₋₈     cycloalkyl, wherein cycloalkyl is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, heterocyclyl, wherein     heterocyclyl is 3-, 4-, 5-, 6- or 7-membered and is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, aryl,     wherein aryl is unsubstituted or mono- or polysubstituted, or     heteroaryl, wherein heteroaryl is unsubstituted or mono- or     polysubstituted, or R⁶ and R⁷ together form Q, wherein Q means     γ′-CR¹⁵═CR¹⁶—CR¹⁷═CR¹⁸-δ′, the end of Q marked γ′ is attached to the     γ carbon atom of the compound of the general formula I and the end     of Q marked δ′ is attached to the δ carbon atom of the compound of     the general formula I, and R⁸ and R⁹ are defined as above, or R⁶ and     R⁹ together form T, wherein T means γ′-CR¹⁹═CR²⁰—CR²¹═CR²²-ε′ or     γ′-N═CR²⁰—CR²¹═N-ε′, the end of T marked γ′ is attached to the γ     carbon atom of the compound of the general formula I and the end of     T marked ε′ is attached to the ε carbon atom of the compound of the     general formula I, and R⁷ and R⁸ are defined as above, or R⁸ and R⁹     together form U, wherein U means η′-CR¹⁹═CR²⁰—CR²¹═CR²²-ε′, the end     of U marked η′ is attached to the η carbon atom of the compound of     the general formula I and the end of U marked ε′ is attached to the     ε carbon atom of the compound of the general formula I, and R⁶ and     R⁷ are defined as above, -   R¹⁰ means C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, aryl,     wherein aryl is unsubstituted or mono- or polysubstituted,     heteroaryl, wherein heteroaryl is unsubstituted or mono- or     polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, -   R¹¹ means NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl),     N((C₁₋₆ alkyl)aryl)₂, C₁₋₈ alkyl, wherein alkyl is linear or     branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, aryl, wherein aryl is unsubstituted or mono- or     polysubstituted, heteroaryl, wherein heteroaryl is unsubstituted or     mono- or polysubstituted, (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and aryl is unsubstituted     or mono- or polysubstituted, or (C₁₋₆ alkyl)heteroaryl, wherein C₁₋₆     alkyl is linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted and heteroaryl is     unsubstituted or mono- or polysubstituted, -   R¹² means C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, C₃₋₈ cycloalkyl, wherein cycloalkyl is saturated or     unsaturated and is unsubstituted or mono- or polysubstituted, (C₁₋₆     alkyl)aryl, wherein C₁₋₆ alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, -   R¹³ means C(═O)CH₃, C(═O)phenyl, C(═O)O-t.-butyl (t-BOC), -   R¹⁴ means H, NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆     alkyl)aryl), N((C₁₋₆ alkyl)aryl)₂, C₁₋₈ alkyl, wherein alkyl is     linear or branched and is saturated or unsaturated and is     unsubstituted or mono- or polysubstituted, C₃₋₈ cycloalkyl, wherein     cycloalkyl is saturated or unsaturated and is unsubstituted or mono-     or polysubstituted, aryl, wherein aryl is unsubstituted or mono- or     polysubstituted, or (C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear     or branched and is saturated or unsaturated and is unsubstituted or     mono- or polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, OC₁₋₈ alkyl, wherein alkyl is linear or branched     and is saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, OC₃₋₈ cycloalkyl, wherein cycloalkyl is saturated     or unsaturated and is unsubstituted or mono- or polysubstituted,     Oaryl, wherein aryl is unsubstituted or mono- or polysubstituted, or     O—(C₁₋₆ alkyl)aryl, wherein C₁₋₆ alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted and aryl is unsubstituted or mono- or     polysubstituted, -   R¹⁵, R¹⁶, R¹⁷ and R¹⁸ mutually independently mean H, F, Cl, Br, I,     CN, OH, C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, or CO₂H, and -   R¹⁹, R²⁰, R²¹ and R²² mutually independently mean H, F, Cl, Br, I,     CN, OH, C₁₋₈ alkyl, wherein alkyl is linear or branched and is     saturated or unsaturated and is unsubstituted or mono- or     polysubstituted, or CO₂H.

The substance library according to the invention preferably contains at least 40 compounds, particularly preferably at least 80 and in particular at least 120 compounds of the general formula I as defined above.

For the purposes of the present invention, a “substance library” is taken to mean a group of compounds which are produced using the same process under identical or virtually identical reaction conditions while varying one or more reagents. Such a substance library may contain the members of the library both as individual pure compounds and as a mixture of said compounds. Using this substance library, it is possible, for example, to carry out automated medical screening in one or more in vitro screening processes.

The present invention furthermore also provides a pharmaceutical preparation or composition which comprises at least one of the above-defined compounds according to the invention of the general formula I or the pharmaceutically acceptable salts thereof. Compounds suitable for the pharmaceutical composition include 6-chloro-2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(2-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-(4-tolyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-chlorophenyl)-4-(4-totyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-(2-hydroxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-propyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-propyl-2,3,3a,4,5,10a-hexahydro-2H-pyrido[1,2-a]furo[3,2-e]pyrimidine and/or 4-propyl-2,4,4a,5,6,11a-hexahydro-2H-pyrido[1,2-a]pyrano[3,2-e]pyrimidine.

These compounds may be present in the pharmaceutical preparation according to the invention not only as isomerically pure, in particular enantiomerically pure or diastereomerically pure, compounds but also as a racemic or non-racemic mixture. It is preferred for the pharmaceutical preparation to contain a pharmaceutically acceptable salt of the compounds according to the invention, in particular a hydrochloride.

The present invention also provides the use of at least one compound according to the invention of the general formula I, including the diastereomers or enantiomers thereof, also as racemates or an enantiomeric mixture in the form of the free base thereof or of a salt formed with a physiologically acceptable acid, in particular in the form of the hydrochloride salt, for the production of a pharmaceutical preparation the treatment of pain. The compounds according to the invention have proved to be analgesically active.

It has surprisingly been found that the compounds according to the invention of the general formula I are highly suitable for further indications, in particular for the treatment of urinary incontinence, pruritus, tinnitus and/or diarrhea. The present application accordingly also provides the use of at least one compound according to the invention of the general formula I, including a pharmaceutically acceptable salt for the production of a pharmaceutical preparation for the treatment of urinary incontinence, pruritus, tinnitus and/or diarrhea.

The present invention furthermore provides pharmaceutical compositions which contain at least one compound of the above-defined general formula I or of a pharmaceutically acceptable salt thereof and one or more pharmaceutical auxiliary substances.

The pharmaceutical preparations and pharmaceutical compositions according to the invention may be liquid, semi-solid or solid dosage forms and assume the form of and be administered as, for example, solutions for injection, drops, succi, syrups, sprays, suspensions, granules, tablets, pellets, transdermal therapeutic systems, capsules, dressings, suppositories, ointments, creams, lotions, gels, emulsions or aerosols and, depending upon the presentation, they contain, in addition to at least one compound according to the invention of the general formula I, pharmaceutical auxiliary substances, such as excipients, fillers, solvents, diluents, surface-active substances, dyes, preservatives, suspending agents, slip additives, lubricants, flavors and/or binders. These auxiliary substances may be, for example: water, ethanol, 2-propanol, glycerol, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glucose, fructose, lactose, sucrose, dextrose, molasses, starch, modified starch, gelatine, sorbitol, inositol, mannitol, microcrystalline cellulose, methylcellulose, carboxymethylcellulose, cellulose acetate, shellac, cetyl alcohol, polyvinylpyrrolidone, paraffins, waxes, natural and synthetic gums, gum arabic, alginates, dextran, saturated and unsaturated fatty acids, stearic acid, magnesium stearate, zinc stearate, glyceryl stearate, sodium lauryl sulfate, edible oils, sesame oil, coconut oil, peanut oil, soya oil, lecithin, sodium lactate, polyoxyethylene and polyoxypropylene fatty acid esters, sorbitan fatty acid esters, sorbic acid, benzoic acid, citric acid, ascorbic acid, tannic acid, sodium chloride, potassium chloride, magnesium chloride, calcium chloride, magnesium oxide, zinc oxide, silicon dioxide, titanium oxide, titanium dioxide, magnesium sulfate, zinc sulfate, calcium sulfate, potash, calcium phosphate, dicalcium phosphate, potassium bromide, potassium iodide, talcum, kaolin, pectin, crospovidone, agar and bentonite.

The auxiliary substances and the quantities thereof which are to be used are selected depending on whether the pharmaceutical preparation is to be administered orally, subcutaneously, parenterally, intravenously, vaginally, pulmonally, intraperitoneally, transdermally, intramuscularly, nasally, buccally, rectally or topically, for example onto infections of the skin or mucous membranes and into the eyes. Preparations in the form of tablets, coated tablets, capsules, granules, drops, succi and syrups are, inter alia, suitable for oral administration, while solutions, suspensions, readily reconstitutible powders for inhalation and sprays are suitable for parenteral, topical and inhalatory administration. Compounds according to the invention of the general formula I in a depot in dissolved form or in a dressing, optionally with the addition of skin penetration promoters, are suitable percutaneous administration preparations. Rectally, transmucosally, parenterally, orally or percutaneously administrable formulations may release the compounds according to the invention of the general formula I in delayed manner.

The pharmaceutical preparations and pharmaceutical compositions according to the invention are produced using means, devices, methods and processes well known to an ordinarily skilled person from the art of pharmaceutical formulation, as are described, for example, in “Remington's Pharmaceutical Sciences”, ed. A. R. Gennaro, 17th edition, Mack Publishing Company, Easton, Pa. (1985), in particular in part 8, sections 76 to 93.

Thus, for example, for a solid formulation such as a tablet, the active ingredient of the pharmaceutical preparation, i.e. a compound of the general formula I or a pharmaceutically acceptable salt thereof, may be granulated with a pharmaceutical excipient, for example conventional tablet ingredients, such as maize starch, lactose, sucrose, sorbitol, talcum, magnesium stearate, dicalcium phosphate or pharmaceutically acceptable gums, and pharmaceutical diluents, such as water, in order to form a solid composition which contains a compound according to the invention or a pharmaceutically acceptable salt thereof in homogeneously dispersed manner. Homogeneously dispersed is here taken to mean that the active ingredient is uniformly dispersed throughout the composition, such that the latter may straightforwardly be subdivided into unit dosage forms containing an equal amount of the active ingredient, such as tablets, pills or capsules. The solid composition is then subdivided into unit dosage forms. The tablets or pills of the pharmaceutical preparation according to the invention or of the pharmaceutical compositions according to the invention may also be coated or compounded in another manner in order to provide a dosage form with delayed release. Suitable coating compositions are, inter alia, polymeric acids and mixtures of polymeric acids with materials such as, for example shellac, cetyl alcohol and/or cellulose acetate.

The quantity of active substance to be administered to the patient varies and is a function of the weight, age and medical history of the patient, the mode of administration, the indication and the severity of the condition. Conventionally, at least one compound according to the invention of the general formula I is administered in a quantity of 0.1 to 5000 mg/kg, in particular of 1 to 500 mg/kg, preferably of 2 to 250 mg/kg body weight.

The purpose of the following Examples is to illustrate the present invention in greater detail.

EXAMPLES

The chemicals and solvents used were purchased from one of the following suppliers: Acros, Geel; Avocado, Port of Heysham; Aldrich, Deisenhofen; Fluka, Seelze; Lancaster, Mülheim; Maybridge, Tintagel; Merck, Darmstadt; Sigma, Deisenhofen; TCI, Japan; or were produced in accordance with processes generally known in the art.

Chromatographic purification was performed on an HPLC-RP-18 column from Macherey-Nagel; material NUCLEOSIL 100-3 C₁₈—HD, approx. 100 mm (VarioPrep), internal diameter 21 mm; mobile solvent water/methanol, gradient: 50–100% in approx. 18 min., flow rate: 10 ml/min; detection: UV, Beckman 168 PDA.

General Procedure, GP(Semi-Automated Synthesis)

A stirrer was placed in a round-bottomed glass tube (diameter 16 mm, length 125 mm) with a thread and the tube sealed using a screw lid with septum. The tube was placed in a stirring block, which had been adjusted to 20° C. The following reagents were then added in succession by pipette:

1 ml of a solution of trifluoroacetic acid, 0.1 M, and heteroarylamine component II, 0.1 M, in acetonitrile;

-   1 ml of a 0.11 M solution of the aldehyde III in acetonitrile; -   1 ml of a 0.3 M solution of the olefin IV in acetonitrile.

The reaction mixture was stirred for 10 hours at 20° C. in one of the stirring blocks. The reaction solution was then filtered off. The tube was here rinsed twice with 1.5 ml portions of a 7.5% NaHCO₃ solution.

The rack containing the samples was placed manually on the working up unit. The reaction mixture was combined with 2 ml of ethyl acetate on a vortexer and shaken. The mixture was briefly centrifuged in the centrifuge to form a phase boundary. The phase boundary was detected optically and the organic phase removed by pipette. In the next step, the aqueous phase was again combined with 2 ml of ethyl acetate, shaken, centrifuged and the organic phase removed by pipette. The combined organic phases were dried over 2.4 g of MgSO₄ (pellets). The solvent was removed in a vacuum centrifuge.

Each sample was characterized by ESI-MS and/or NMR. Mass spectrometric investigation (ESI-MS) was carried out using a Finnegan LCQ Classic mass spectrometer. ¹H-NMR investigations of the compounds according to the invention were carried out with a 300 MHz Bruker DPX Advance NMR spectrometer.

Examples 1–131 (see Table 1) were produced in accordance with the above general procedure. Examples 80 to 89 were worked by means of reversed-phase (RP) HPLC.

TABLE 1 Calculated Example mass Actual mass Compound 1 400.78 401.2/403.2 9-chloro-4-(4-methyoxyphenyl)-3-methyl-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 2 428.83 429.2/430.1 9-chloro-4-(4-methyoxyphenyl)-3-methyl-7-trifluoromethyl-3,4- dihydro-2H-pyridol[1,2-a]pyrimidine 2-carboxylic acid ethyl ester 3 411.28 411.1/413.1 7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester 4 500.19 499.1/501.0/503.0 7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester 5 387.39 388.2 4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid ethyl ester 6 381.25 381.1/383.0 7,9-dichloro-4-(4-methyoxyphenyl)-3,4-dihydro-2H-pyridol[1,2- a]pyrimidine 2-carboxylic acid ethyl ester 7 357.36 358.2 4-(4-methyoxyphenyl)-7-nitro-3,4-dihydro-2H-pyridol[1,2- a]pyrimidine 2-carboxylic acid ethyl ester 8 383.23 383.2/385.0 7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 9 486.16 485.1/487.0/488.9 7,9-dibromo-4-(3,4-dimethyoxyphenyl)-6-methyl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 10 359.33 360.1 4-(3,4-dimethyoxyphenyl)-7-nitro-3,4-dihydro-2H-pyridol[1,2- a]pyrimidine 2-carboxylic acid 11 353.2 353.1/355.0 7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 12 329.31 330.1 4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 13 408.21 408.1/410.1 7-bromo-4-(4-methyoxyphenyl)-9-nitro-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 14 450.27 450.2/452.1 7,9-dichloro-4-(3,4-dimethoxyphenyl)-2-(5-nitro-2-furanyl)- 3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 15 539.18 538.1/540.1/542.0 7,9-dibromo-4-(3,4-dimethoxyphenyl)-2-(5-nitro-2-furanyl)- 3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 16 426.38 427.2 4-(3,4-dimethoxyphenyl)-7-nitro-2-(5-nitro-2-furanyl)-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 17 420.25 420.2/422.1 7,9-dichloro-4-(4-methoxyphenyl)-2-(5-nitro-2-furanyl)-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 18 419.35 419.3/421.1 2-[7,9-dichloro-4-(2,4-dimethylphenyl)-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 19 452.9 453.3 2-[9-chloro-4-(2,4-dimethylphenyl)-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 20 540.26 539.3/541.1/543.1 2-[7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 21 421.32 421.1/423.1 2-[7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 22 510.23 509.1/511.0/513.0 2-[7,9-dibromo-4-(4-methoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 23 454.87 455.2/456.0/457.1 2-[9-chloro-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 24 397.43 398.2 2-[4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]- 2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 25 357.36 358.2 4-(4-hydroxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester 26 355.24 355.1/357.0 7,9-dichloro-4-phenylsulfanyl-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 27 331.34 332.1 7-nitro-4-phenylsulfanyl-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 28 383.23 383.1/385.1 7,9-dichloro-4-(4-hydroxy-3-methyoxyphenyl)-3-methyl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 29 472.14 471.0/473.0/475.0 7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 30 486.16 485.0/487.0/488.9 7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl-34- dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 31 416.78 417.1/419.1 9-chloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-7- trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2- carboxylic acid 32 367.23 367.1/369.1 7,9-dichloro-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 33 456.14 455.0/457.0/459.0 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 34 470.17 469.0/471.0/472.9 7,9-dibromo-4-(4-methoxyphenyl)-3,6-dimethyl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 35 400.78 401.1/403.1 9-chloro-4-(4-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 36 343.33 344.2 4-(4-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 37 422.23 422.1/424.0 7-bromo-4-(4-methoxyphenyl)-3-methyl-9-nitro-34-dihydro- 2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 38 353.2 353.1/355.1 7,9-dichloro-4-(4-hydroxyphenyl)-3-methyl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 39 456.14 455.0/457.0/459.0 7,9-dibromo-4-(4-hydroxyphenyl)-3,6-dimethyl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 40 383.23 383.1/385.1 7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 41 472.14 471.0/473.0/475.0 7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 42 486.16 485.0/487.0/489.0 7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 43 416.78 417.1 9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 44 359.33 360.2 4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 45 285.3 286.2 4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrazine[1,2- a]pyrimidine 2-carboxylic acid 46 353.2 353.1/355.1 7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 47 442.11 441.0/443.0/445.0 7,9-dibromo-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 48 456.14 455.0/457.0/459.0 7,9-dibromo-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid 49 386.75 387.1 9-chloro-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid 50 329.31 330.1 4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 2-carboxylic acid 51 443.32 441.2/443.1/445.1 [7,9-dichloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4- dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 52 532.24 533.0 [7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4- dihydro-2H-pyrido[1,2-a9 -2-pyrimidinyl]-phenylmethanone 53 546.26 545.0/547.0/549.0 [7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl- 3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 54 419.43 420.2 [4-(4-hydroxy-3-methoxyphenyl)-3-methyl-7-nitro-3,4- dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 55 403.43 404.2 [4-(4-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 56 516.24 515.0/517.0/519.0 [7,9-dibromo-4-(4-hydroxyphenyl)-3,6-dimethyl-3,4-dihydro- 2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 57 443.32 443.1/445.1 [7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 58 532.24 531.1/533.1 [7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 59 546.26 545.1/547.0 [7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro- 2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 60 476.88 477.1 [9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone 61 419.43 420.2 [4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2- a]-2-pyrimidinyl]-phenylmethanone 62 389.41 390.2 [4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2- pyrimidinyl]-phenylmethanone 63 303.18 303.1/305.1 2-(7,9-dichloro-2-cyclopropyl-3,4-dihydro-2H-pyrido[1,2-a]-4- pyrimidinyloxy)-ethanol 64 392.1 391.0/393.0/395.0 2-(7,9-dibromo-2-cyclopropyl-3,4-dihydro-2H-pyrido[1,2-a]-4- pyrimidinyloxy)-ethanol 65 336.74 337.1/339.1 2-(9-chloro-2-cyclopropyl-7-trifluoromethyl-3,4-dihydro-2H- pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol 66 279.29 280.1 2-(2-cyclopropyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-4- pyrimidinyloxy)-ethanol 67 412.83 413.1 9-chloro-2-cyclopropyl-4-(3,4-dimethoxyphenyl)-7- trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 68 438.17 439.0 7,9-dibromo-2-cyclopropyl-4-(4-methoxyphenyl)-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 69 382.81 383.1/385.1 9-chloro-2-cyclopropyl-4-(4-methoxyphenyl)-7- trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 70 325.36 326.2 2-cyclopropyl-4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 71 345.26 345.1/347.1 2-(7,9-dichloro-2-cyclohexyl-3,4-dihydro-2H-pyrido[1,2-a]-4- pyrimidinyloxy)-ethanol 72 434.18 433.1/435.1/437.0 2-(7,9-dibromo-2-cyclohexyl-3,4-dihydro-2H-pyrido[1,2-a]-4- pyrimidinyloxy)-ethanol 73 448.2 447.1/449.0/451.0 2-(7,9-dibromo-2-cyclohexyl-6-methyl-3,4-dihydro-2H- pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol 74 378.82 379.2/381.2 2-(9-chloro-2-cyclohexyl-7-trifluoromethyl-3,4-dihydro-2H- pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol 75 321.37 322.2 2-(2-cyclohexyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-4- pyrimidinyloxy)-ethanol 76 421.36 421.1/423.1 7,9-dichloro-2-cyclohexyl-4-(3,4-dimethoxyphenyl)-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 77 391.34 391.1/393.1 7,9-dichloro-2-cyclohexyl-4-(4-methoxyphenyl)-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 78 480.25 479.1/481.1/483.0 7,9-dibromo-2-cyclohexyl-4-(4-methoxyphenyl)-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 79 424.89 425.2/427.2 9-chloro-2-cyclohexyl-4-(4-methoxyphenyl)-7-trifluoromethyl- 3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 80 484.19 485.0/487.0 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester 81 456.14 457.4/459.5 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H pyrido[1,2-a]pyrimidine 2-carboxylic acid 82 523.19 522.4/524.3/526.2 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-2-(5-nitro-2- furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 83 524.26 525.2 2-[7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro- 2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 84 553.21 554.2/555.2/556.2 7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-2-(5-nitro-2- furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 85 396.35 397.1 4-(4-methoxyphenyl)-7-nitro-2-(5-nitro-2-furanyl)3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 86 508.26 509.1 2-[7,9-dibromo-4-(2,4-dimethylphenyl)-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 87 554.28 553.2/555.1/557.1 2-[7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4- dihydro-2H-pyrido]1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 88 484.9 485.5 2-[9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 89 524.26 525.1/527.2 2-[7,9-dibromo-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro- 2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 90 399.42 400.2 2-[4-(4-fluorophenyl)-4-methyl-7-nitro-3,4-dihydro-2H- pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester 91 393.51 291.3 (M+H− 9-benzyloxy-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H- Obenzyl) pyrido[1,2-a]pyrimidine 92 346.41 347.3 8-methyl-7-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 93 356.28 356.2/358.2 7,9-dichloro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 94 389.83 390.3/392.2 9-chloro-4-phenyl-2-pyridin-2-yl-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 95 346.41 347.1 8-methyl-9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 96 332.38 333.2 7-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 97 332.38 333.2 9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine 98 411.28 413.1/416.2 7-bromo-9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 99 459.2 458.1/460.0/462.0 7,9-dibromo-6-methyl-4-phenyl-2-pyridin-2-yl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 100 445.18 444.2/446.1/448.0 7,8-dibromo-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 101 363.44 364.2 4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2- a]pyrimidine-9-carboxylic acid 102 333.45 334.2 7-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 103 425.55 426.2 9-benzyloxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 104 378.45 379.2 8-methyl-7-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 105 398.87 399.1/400.0 6-chloro-9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 106 388.32 388.2/390.1 7,9-dichloro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 107 421.88 422.2/424.1/425.1 9-chloro-4-phenylsulfanyl-2-pyridin-2-yl-7-trifluoromethyl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 108 378.45 379.2 8-methyl-9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 109 364.42 365.2 7-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 110 398.33 398.1/400.1/401.1 7-bromo-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 111 364.42 365.2 9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 112 412.36 414.1/415.1 7-bromo-9-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4- dihydro-2H-pyrido[1,2-a[pyrimidine 113 412.36 414.1 4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido]1,2-a]- 9-pyrimidinol 114 335.43 353.2/356.1 7-chloro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- (M + H₂O) pyrido[1,2-a]pyrimidine 115 335.43 336.2 4-phenylsulfanyl-6-propyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 116 491.25 492.1 7,9-dibromo-6-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4- dihydro-2H-pyrido[1,2-a]pyrimidine 117 387.43 388.2 4-phenylsulfanyl-2-pyridin-2-yl-7-trifluoromethyl-3,4-dihydro- 2H-pyrido[1,2-a]pyrimidine 118 477.23 476.1/478.0/480.0 7,9-dibromo-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H- pyrido[1,2-a]pyrimidine 119 385.49 386.2 1-phenylsulfanyl-3-pyridin-2-yl-2,3-dihydro-1H- pyrimidine[1,2-a]-10-quinolinol 120 289.39 288.4 2-methyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro- 6H-pyridol[1,2-a]quinazoline 121 344.26 344.3/361.2/363.2 2,4-dichloro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a- (M + H₂O) tetrahydro-6H-pyrido[1,2-a]quinazoline 122 377.81 378.3/395.2/397.1 4-chloro-6-pyridin-2-yl-2-trifluoromethyl-7,10-methano- (M + H₂O) 6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline 123 320.35 338.2 (M + H₂O) 2-nitro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro- 6H-pyrido[1,2-a]quinazoline 124 320.35 338.2 (M + H₂O) 4-nitro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro- 6H-pyrido[1,2-a]quinazoline 125 309.81 307.4/327.2 2-chloro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro- (M + H₂O) 6H-pyrido[1,2-a]quinazoline 126 317.45 335.3 (M + H₂O) 1-propyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro- 6H-pyrido[1,2-a]quinazoline 127 447.18 446.2/448.2/450.1 2,4-dibromo-1-methyl-6-pyridin-2-yl-7,10-methano- 6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline 128 343.36 361.2 (M + H₂O) 6-pyridin-2-yl-2-trifluoromethyl-7,10-methano-6a,7,10,10a- tetrahydro-6H-pyrido[1,2-a]quinazoline 129 341.43 324.1 1,4-methano-5-pyridin-2-yl-1,4a,5,12c-tetrahydro-4H-6,12b- diaza-benzo[c]-12-phenathrenol 130 325.42 324.2 1,4-methano-5-pyridin-2-yl-1,4a,5,12c-tetrahydro-4H-6,12b- diaza-benzo[c]phenathrene 131 325.42 324.2 6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H- isoquino[2,1-a]quinazoline Pharmaceutical Formulation of a Pharmaceutical Preparation According to the Invention

1 g of the hydrochloride of 4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid was dissolved in 1 l of water for injection at room temperature and then adjusted to isotonic conditions by addition of sodium chloride. 

1. A compound of formula I

in which R¹ and R² independently of each other is H; OR¹⁰; SH; SR¹⁰; C₁₋₁₂ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; C³⁻⁸ cycloalkyl, which is saturated or unsaturated, and unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; heteroaryl, which is unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and is unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted; or (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the heteroaryl is unsubstituted or mono- or polysubstituted, wherein one of R¹ and R² is H and the other of R¹ and R² is not H, provided that, if one of R¹ and R² is aryl, then the other of R¹ and R² is H or C₁₋₁₂ alkyl, R³ and R⁴ independently of each other is H; C₁₋₁₂ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, wherein the cycloalkyl is saturated or unsaturated, and unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; heteroaryl, which is unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted; or (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the heteroaryl is unsubstituted or mono- or polysubstituted, wherein at least one of R³ and R⁴ is H, or one of R¹ or R², together with one of R³ or R⁴, forms W, wherein W means α′-(CH₂)_(n)-β′ where n=3, 4, 5, 6, 7, 8, 9 or 10; α′-CH═CH—CH₂-β′; α′CH═CH—CH₂—CH₂-β′; α′-CH₂—CH═CH—CH₂-β′; α′-CH₂—CH₂—CH═CH—CH₂—CH₂-β′; α′-O—(CH₂)_(n)-β′ where n=2, 3, 4, 5 or 6;

where X=CH₂, O or S,

and the end of W marked & is attached to the a carbon atom of the compound of the general formula I and the end of W marked α is attached to the α carbon atom of the compound of formula I, the other of R¹ and R² is H or C₁₋₁₂ alkyl, wherein the alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the other of R³ and R⁴ is H or C₁₋₁₂ alkyl, wherein the alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, R⁵ is C₁₋₁₂ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, which is saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; heteroaryl, which is unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the heteroaryl is unsubstituted or mono- or polysubstituted; C(═O)R¹¹; CO₂H; or CO₂R¹², R⁶, R⁷, R⁸ and R⁹ independently of each other is H, F, Cl, Br, I, CN, NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alikyl)₂, NH((C₁₋₆ alkyl)aryl), N((C₁₋₆ alkyl)aryl)₂, NHR¹³, NO₂, OH, SH, O—C₁₋₈ alkyl or S(O)_(p)—C₁₋₈ alkyl, wherein the alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and p is 0, 1 or 2; O-aryl or S(O)_(q)-aryl, which is unsubstituted or mono- or polysubstituted, and q is 0, 1 or 2; O—(C₁₋₆ alkyl)aryl or S(O)_(r)—(C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, the aryl is unsubstituted or mono- or polysubstituted, and r is 0, 1 or 2; CO₂H; C(═O)R¹⁴; C₁₋₁₂ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; CF₃; C₃₋₈ cycloalkyl, which is saturated or unsaturated, unsubstituted or mono- or polysubstituted; heterocyclyl, which is 3-, 4-, 5-, 6- or 7-membered, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; or heteroaryl, which is unsubstituted or mono- or polysubstituted; or R⁶ and R⁷ together form Q, wherein Q means γ′-CR¹⁵═CR¹⁶—CR¹⁷═CR¹⁸-δ′, the end of Q marked γ′ is attached to the γ carbon atom of the compound of formula I and the end of Q marked δ′ is attached to the δ carbon atom of the compound of formula I, and R⁸ and R⁹ are defined as above, or R⁶ and R⁹ together form T, wherein T means γ′-CR¹⁹═CR²⁰—CR²¹═CR²²-ε′ or γ′-N═CR²⁰—CR²¹═N-ε′, the end of T marked γ′ is attached to the γ carbon atom of the compound of formula I and the end of T marked ε is attached to the ε carbon atom of the compound of formula I, and R⁷ and R⁸ are defined as above, or R⁸ and R⁹ together form U, wherein U means η′-CR¹⁹═CR²⁰—CR²¹═CR²²—ε′, the end of U marked η is attached to the η carbon atom of the compound of formula I and the end of U marked ε′ is attached to the ε carbon atom of the compound of formula I, and R⁶ and R⁷ are defined as above, R¹⁰ is C₁₋₈ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, which is saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; heteroaryl, which is unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted; or (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the heteroaryl is unsubstituted or mono- or polysubstituted, R¹¹ means NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl), N((C₁₋₆ alkyl)aryl)², C₁₋₈ alkyl, wherein the alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, which is saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; heteroaryl, which is unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted; or (C₁₋₆ alkyl)heteroaryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the heteroaryl is unsubstituted or mono- or polysubstituted; R¹² means C₁₋₈ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, which is saturated or unsaturated, unsubstituted or mono- or polysubstituted; (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted, R¹³ means C(═O)CH₃, C(═O)phenyl, C(═O)O-t.-butyl (t-BOC), R¹⁴ means H, NH₂, NH(C₁₋₆ alkyl), N(C₁₋₆ alkyl)₂, NH((C₁₋₆ alkyl)aryl), N((C₁₋₆ alkyl)aryl)₂, C₁₋₈ alkyl, wherein the alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; C₃₋₈ cycloalkyl, which is saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; or (C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted; OC₁₋₈ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; OC₃₋₈ cycloalkyl, which is saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl, which is unsubstituted or mono- or polysubstituted; or O—(C₁₋₆ alkyl)aryl, wherein the C₁₋₆ alkyl is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted, and the aryl is unsubstituted or mono- or polysubstituted, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ mutually independently mean H, F, Cl, Br, I, OH, CN; C₁₋₈ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; CO₂H, and R¹⁹, R²⁰, R²¹ and R²² mutually independently mean H, F, Cl, Br, I, CN, OH, C₁₋₈ alkyl, which is linear or branched, saturated or unsaturated, and unsubstituted or mono- or polysubstituted; or CO₂H, or a pharmaceutically acceptable salt thereof, provided that the following compounds are excluded: 6-chloro-2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(2-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-(4-tolyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-chlorophenyl)-4-(4-tolyl) -3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-(2-hydroxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-propyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-propyl-2,3,3a,4,5,10a-hexahydro-2H-pyrido[1,2-a]furo[3,2-e]pyrimidine, and 4-propyl-2,4,4a,5,6,11a-hexahydro-2H-pyrido[1,2-a]pyrano[3,2-e]pyrimidine.
 2. A compound according to claim 1, in the form of a racemate or a mixture of diastereomers or a mixture of enantiomers in any mixing ratio.
 3. A compound according to claim 1, in the form of a pure enantiomer or a pure diastereomer.
 4. A compounds according to claim 1, wherein one of R¹ and R² is OR¹⁰, SR¹⁰, C₁₋₆ alkyl or aryl, one of R³ and R⁴ is H or C₁₋₆ alkyl, or one of R¹ and R² together with one of R³ and R⁴ form W, wherein W means

and the other two residues of R¹, R², R³ and R⁴ mean H or C₁₋₆ alkyl, R⁵ is C₃₋₆ cycloalkyl, heteroaryl, C(═O)R¹¹, CO₂H or CO₂R¹², R⁶ is H, F, Cl, Br, CN, NO₂, C(═O)R¹⁴, C₁₋₆ alkyl, CF₃ or aryl, R⁷ is H, F, Cl, Br, CN, NH₂, OH or C₁₋₆ alkyl, or R⁶ and R⁷ together form Q, wherein Q means γ′-CR¹⁵═CR¹⁶—CR¹⁷═CR¹⁸-δ′, R⁸ means H, F, Cl, Br, CN, NO₂, O—(C₁₋₆ alkyl)aryl, CO₂H, CONH₂ or C₁₋₆ alkyl, R⁹ means H, OH, CF₃ or C₁₋₆ alkyl, or R⁸ and R⁹ together form U, wherein U means ε′-CH═CH—CH═CH-η′, R¹⁰ means C₁₋₈ alkyl or aryl, R¹¹ means aryl, R¹² means C₁₋₆ alkyl, R¹⁴ means OC₁₋₆ alkyl, and one of R¹⁵, R¹⁶, R¹⁷ and R¹⁸ means H or OH and the other residues of R¹⁵, R¹⁶, R¹⁷ and R¹⁸ mean H.
 5. A compound according to claim 4, wherein one of R¹ and R² is O—(CH₂)₂—OH, S-phenyl, CH₃, phenyl, 3-methyiphenyl, 2,4-dimethyiphenyl, 4-fluorophenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 4-hydroxy-3-methoxyphenyl or 2-naphthyl, one of R³ and R⁴ is H or methyl, or one of R¹ and R² together with one of R³ and R⁴ form W, wherein W means

and the other two of R¹, R², R³ and R⁴ are H, R⁵ is cyclopropyl, 2-(C(═O)O-ethyl)-cyclopropyl, cyclohexyl, 2-pyridinyl, 5-methyl-2-furanyl, 5-nitro-2-furanyl, C(═O)phenyl, CO₂H or CO₂ ethyl, R⁶ is H, Cl, Br, CN, NO₂, CO₂ethyl, methyl, CF₃ or phenyl, R⁷ is H, Cl, CN, NH₂, OH, methyl or n-propyl, or R⁶ and R⁷ together form Q, wherein Q is γ′-CH═CH—CH═CR¹⁸-δ′, R⁸ is H, Cl, Br, NO₂, OH, O—CH₂phenyl, CO₂H or methyl, R⁹ is H or methyl, or R⁸ and R⁹ together form U, wherein U means ε′-CH═CH—CH═CH—η′, and R¹⁸ means H or OH.
 6. A compound according to claim 1, selected from the group consisting of: 9-chloro-4-(4-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 9-chloro-4-(4-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester, 7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester, 7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester, 4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester, 7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime 2-carboxylic acid ethyl ester, 4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester, 7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime 2-carboxylic acid, 7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime 2-carboxylic acid, 4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime 2-carboxylic acid, 7-bromo-4-(4-methoxyphenyl)-9-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dichloro-4-(3,4-dimethoxyphenyl)-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-4-(3,4-dimethoxyphenyl)-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime, 4-(3,4-dimethoxyphenyl)-7-nitro-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dichloro-4-(4-methoxyphenyl)-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime, 2-[7,9-dichloro-4-(2,4-dimethyiphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-2-yl]-cyclopropane carboxylic acid ethyl ester, 2-[9-chloro-4-(2,4-dimethylphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-2-yl]-cycloprop ane carboxylic acid ethyl ester, 2-[7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cycloprop ane carboxylic acid ethyl ester, 2-[7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester, 2-[7,9-dibromo-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester, 2-[9-chloro-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cycloprop ane carboxylic acid ethyl ester, 2-[4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester, 4-(4-hydroxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester, 7,9-dichloro-4-phenylsulfanyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7-nitro-4-phenylsulfanyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dichloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 9-chloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dichloro-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime 2-carboxylic acid ethyl ester, 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-methoxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 9-chloro-4-(4-methoxyphenyl)-3-methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 4-(4-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7-bromo-4-(4-methoxyphenyl)-3-methyl-9-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dichloro-4-(4-hydroxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-hydroxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime 2-carboxylic acid, 7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 9-chioro -4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dichloro-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 9-chioro-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, [7,9-dichloro-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [7,9-dibromo-4-(4-hydroxy-3-methoxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1 2-a]-2-pyrimidinyl]-phenylmethanone [4-(4-hydroxy-3-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [4-(4-methoxyphenyl)-3-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [7,9-dibromo-4-(4-hydroxyphenyl)-3,6-dimethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [7,9-dichloro-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [7,9-dibromo-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [4-(3,4-dimethoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, [4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-phenylmethanone, 2-(7,9-dichloro-2-cyclopropyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 2-(7,9-dibromo-2-cyclopropyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 2-(9-chioro -2-cyclopropyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 2-(2-cyclopropyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 9-chloro-2-cyclopropyl-4-(3,4-dimethoxyphenyl)-7-trifluoro methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-2-cyclopropyl-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 9-chloro-2-cyclopropyl-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-cyclopropyl-4-(4-methoxyphenyl)-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(7,9-dichloro-2-cyclohexyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 2-(7,9-dibromo-2-cyclohexyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 2-(7,9-dibromo-2-cyclohexyl-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 2-(9-chloro-2-cyclohexyl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 2-(2-cyclohexyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-4-pyrimidinyloxy)-ethanol, 7,9-dichloro-2-cyclohexyl-4-(3,4-dimethoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dichloro-2-cyclohexyl-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-2-cyclohexyl-4-(4-methoxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 9-chioro-2-cyclohexyl-4-(4-methoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid ethyl ester, 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine 2-carboxylic acid, 7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-[7,9-dibromo-4-(4-methoxyphenyl)-3-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cycloprop ane carboxylic acid ethyl ester, 7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-(4-methoxyphenyl)-7-nitro-2-(5-nitro-2-furanyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-[7,9-dibromo-4-(2,4-dimethylphenyl)-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester, 2-[7,9-dibromo-4-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cycloprop ane carboxylic acid ethyl ester, 2-[9-chloro-4-(3,4-dimethoxyphenyl)-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cyclopropane carboxylic acid ethyl ester, 2-[7,9-dibromo-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cycloprop ane carboxylic acid ethyl ester, 2-[4-(4-fluorophenyl)-4-methyl-7-nitro-3,4-dihydro-2H-pyrido[1,2-a]-2-pyrimidinyl]-cycloprop ane carboxylic acid ethyl ester, 9-benzyloxy-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 8-methyl-7-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dichloro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 9-chloro-4-phe nyl-2-pyridin-2-yl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 8-methyl-9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7-bromo-9-nitro-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-6-methyl-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-4-phenyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-phenylsulfanyl-2-pyridin-2-yl-3,4- dihydro -2H-pyrido[1,2-a]pyrimidine -9-carboxylic acid, 7-methyl-4-phenylsuffanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime, 9-benzyloxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 8-methyl-7-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 6-chloro-9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dichloro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime, 9-chloro-4-phenylsulfanyl-2-pyridin-2-yl-7-trilluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 8-methyl-9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime, 7-bromo-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime, 9-nitro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7-bromo-9-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]-9-pyrimidinol, 7-chloro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidime, 4-phenylsulfanyl-6-propyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-6-methyl-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-phenylsulfanyl-2-pyridin-2-yl-7-trifluoromethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 7,9-dibromo-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 1-phenylsulfanyl-3-pyridin-2-yl-2, 3-dihydro-1H-pyrimidine [1,2-a]-10-quinolinol, 2-methyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 2,4-dichloro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 4-chloro-6-pyridin-2-yl-2-trifluoromethyl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 2-nitro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 4-nitro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 2-chloro-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 1-propyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 2,4-dibromo-1-methyl-6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 6-pyridin-2-yl-2-trifluoromethyl-7,10-methano-6a,7,10,10a-tetrahydro-6H-pyrido[1,2-a]quinazoline, 1,4-methano-5-pyridin-2-yl-1,4a,5,12c-tetrahydro-4H-6,12b-diaza-benzo [c]-12-phenathrenol, 1,4-methano-5-pyridin-2-yl-1,4a,5,12c-tetrahydro-4H-6,12b-diaza-benzo[c]phenathrene, and 6-pyridin-2-yl-7,10-methano-6a,7,10,10a-tetrahydro-6H-isoquino [2,1-a]quinazoline.
 7. A process for producing a compound according to claim 1, the method comprising reacting, in the presence of an acid, a compound of formula II

in which R⁶ and R⁷are as defined for formula I, provided that, if R⁶ and R⁷form Q, the end of Q marked γ′ is attached to the γ carbon atom of formula II and the end of Q marked δ′ is attached to the δ carbon atom of formula II, if R⁶ and R⁹ form T, the end marked γ′ is attached to the γ carbon atom of formula II and the end marked ε′ is attached to the ε carbon atom of formula II, and if R⁸ and R⁹ form U, the end marked η′ is attached to the η carbon atom of formula II and the end marked ε′ is attached to the ε carbon atom of formula II, with a compound of formula III

in which R⁵ is as defined for formula I, and a compound of formula IV

in which R¹, R², R³ and R⁴ are as defined for formula I, provided that, if one of R¹ and R², together with one of R³ and R⁴, forms W, the end of W marked α′ is attached to the α carbon atom of formula IV and the end of W marked β′ is attached to the β carbon atom of formula IV.
 8. A process according to claim 7, wherein the reaction of the compound of formula II with the compound of formula III and the compound of formula IV is performed in a single-vessel reaction.
 9. A process according to claim 7, wherein the acid is trifluoroacetic acid.
 10. A process according to claim 7, wherein the reaction is performed in an organic solvent at a temperature of between about 0 to 100° C. and a reaction time of between about 0.25 to 12 h.
 11. A process according to claim 9, wherein the reaction is performed at a temperature of between about 15 to 40° C.
 12. A process according to claim 10, wherein the organic solvent is acetonitrile.
 13. A substance library comprising at least one compound according to claim
 1. 14. A pharmaceutical preparation comprising at least one compound selected from the group consisting of 6-chloro-2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(2-nitrophenyl)-4-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-nitrophenyl)-4-(4-tolyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 2-(4-chlorophenyl)-4-(4-tolyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-phenyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-(2-hydroxyphenyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-ethoxy-2-propyl-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine, 4-propyl-2,3,3a,4,5,10a-hexahydro-2H-pyrido[1,2-a]furo [3,2-e]pyrimidine, 4-propyl-2,4,4a, 5,6,11a-hexahydro-2H-pyrido[1,2-a]pyrano [3,2-e]pyrimidine, and a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient. 